21 Questions Game to Ask a Guy…

By on August 5, 2014

Getting to know someone new is both exhilarating and scary at the same time. So here’s a little game to make the process less scary and a whole lot more fun! These 21 questions will not only work as a lovely ice breaker when there’s a lull in the conversation  but will also help you learn more about him.

1. If you were an animal, what would you be and why?


This is a great question to ask if you are an animal lover yourself. You will get to know if the guy is interested in dogs or cats (or reptiles!) as much as you are and if things go great, you can have fun walking your little loved ones in the park together.

2. What did you want to be when you were young?


We’ve all had dreams as children. His childhood ambitions could reflect his personality, family values and ideologies. For instance, if he wanted to be a doctor, he could be the caring big brother to his siblings. If he wanted to be a teacher, he’s probably the kind of guy you can count on any time of the day.

3. What is the weirdest thing you have ever eaten?

This will let you know how adventurous and willing to experiment he is. There are men who wouldn’t dare eat anything they are not familiar with (boring!) and then there are men who may be way too adventurous for you. Monkey brains? No, thank you.

4. What is your favorite cartoon character?


His favorite cartoon character could be a reflection of the kind of things he enjoys. Scooby Doo fans may love mystery, Mickey Mouse fans usually love classic humor and so on and so forth.

5. Are you a morning person?

running in the park

Morning people are those who can wake up before the alarm and if your date is one, it means that he likes being productive. But, there’s also nothing wrong with people who are nocturnal. It all comes down to what you prefer.

6. What is your morning ritual like?

His answer to this question will give you an idea of how organized he is. Some men wake up and just go with the flow while some brew their own coffee, read the morning paper and take a hot shower. Admit it, wouldn’t it be nice to wake up to the smell of freshly brewed coffee?

7. What is your favorite movie?


Do you like the same kind of movies? Or would you have to indulge in playful warfare to decide whose choice wins on movie night. It is a win-win situation either way.

8. Have you ever been arrested?

This question will either lead to a “no” or a very interesting story. Keep an open ear and mind. There’s a difference between drunk driving and murder.

9. If you were a woman for a day, what would you do?

wonder woman

Here’s a fun one to see what he thinks the life of a woman is all about. Does he pick something naughty like “sit naked in front of the mirror all day” or something more serious?

10. Describe your most embarrassing moment?

Well, this is mostly a test of honesty. Does he have enough self-confidence to tell you about his most embarrassing moment? If yes, you know he does not really hide his past and can openly talk about it

11.  How many jobs have you had?

working man

This can tell you about any commitment issues that your date may have. If he usually jumps from one job to another and can’t sit still in just one company, he most definitely has a problem with commitment.

12.  What was the last book you read?


Well-read men are amazing in more than one way. They have a thirst for knowledge and that is never a bad thing. In fact, you may even learn a thing or two from them.

13. Do you like what you do for a living?

It’s important for you to know that he actually wanted to pick the profession he’s in and that it wasn’t something that was imposed on him. This shows that your date can make his own decisions and can stand by them.

14.   If you were given the chance to travel to any place in the world, where would it be?


His choice of place for travel will tell you a lot about him. If he wants to go to Rome, he’s probably into arts and history. If he wants to go to a place like Japan, he’s probably into the contemporary arts or technology. If he picks Ibiza, he’s most definitely a party animal.

15.   Are you an optimist, pessimist or a realist?

I believe the more you surround yourself with optimists, the better your life will be. But of course, realists are just as important. Pessimists are a huge no-no.

16.   What sports or physical activities do you do?


Exercise is an important activity for the overall health of a person. Plus, if you know that he is exercising, it means he is disciplined enough to be in shape, which means he’s probably also disciplined in other aspects of his life.

17.  What is the best event you’ve ever attended?

men event

This will show you what kind of activities your date enjoys and what brings him happiness. If it sounds like something you’d enjoy too, well, that’s just the cherry on the cake.

18.   What do you really hate doing?


Does he hate doing the dishes? Does he hate taking out the trash? Does he hate going out partying? Whatever it is, you’ll get an idea of what possible compromises you may have to make in the future (if there is one).

19.  If you could have an unlimited supply of anything, what would it be?

This is a very interesting question because it tells you what your date needs, loves and must have at all costs. It could be food,  other necessities such as electricity or even money!

20.   What’s the one thing you can’t live without and why?


Does he pick his cellphone, or his laptop or his dog? Remember in this case, the “why” is as important as the “what”.

21.   If your life was a movie, what would be the title?

yes man

This would show you how creative your date is with his vocabulary. Plus, it will give you an idea of what his life story is about.

Remember, the 21 questions game is all about having fun. So, ready, get set, PLAY!

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